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Synthesis method of dihydroimidazole compound

A dihydroimidazole and synthesis method technology, applied in chemical instruments and methods, chemical/physical processes, chemical/physical/physical chemical processes, etc., can solve problems such as low reaction efficiency, cumbersome reaction steps, long reaction time, etc., to achieve The effect of speeding up the reaction rate, easy reaction process, and green reaction conditions

Pending Publication Date: 2022-05-06
NANJING ADVANCED BIOLOGICAL MATERIALS & PROCESS EQUIP INST CO LTD
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  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] Purpose of the invention: the present invention aims at the deficiencies in the prior art, and provides a method for synthesizing dihydroimidazole derivatives using a microchannel reaction device, so as to solve the problems of cumbersome reaction steps, long reaction time, and low reaction efficiency in the prior art, Simple and efficient synthesis of dihydroimidazole derivatives using inexpensive metal catalysts

Method used

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  • Synthesis method of dihydroimidazole compound
  • Synthesis method of dihydroimidazole compound
  • Synthesis method of dihydroimidazole compound

Examples

Experimental program
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Effect test

Embodiment 1

[0041]Dissolve 1.5mmol (0.3915g) of (2E,4E)-4-(acetoxyimino)-4-phenylbut-2-enoic acid ethyl ester and 0.1mmol (0.0099g) of cuprous chloride in In 10mL of tetrahydrofuran, the resulting mixed solution was recorded as solution A; 1mmol (0.0930g) of aniline, 2mmol (0.0600g) of paraformaldehyde and 0.4mmol (0.0488g) of 4-methylaminopyridine were dissolved in 10mL of tetrahydrofuran to obtain The mixed solution is denoted as solution B, and then solution A and solution B are pumped in the microchannel reaction device according to the flow volume ratio of 1:1, and the flow rate is respectively 0.2mL / min, and enters the microchannel reactor after being mixed by the Y-type mixer ( The inner diameter of the polytetrafluoroethylene tube of the microreactor is 0.5mm, and the volume of the polytetrafluoroethylene tube is 4mL) to react at 130°C for 20min. The organic phase was obtained from the discharge of the microreactor, and the crude product was obtained by vacuum concentration, which...

Embodiment 2

[0043] 1.5mmol (0.4635g) of (2E,4E)-4-(acetoxyimino)-4-(4-methoxyphenyl)but-2-enoic acid ethyl ester, 0.1mmol (0.0099g) 1mmol (0.0930g) of aniline, 2mmol (0.0600g) of paraformaldehyde and 0.4mmol (0.0488g) of 4-methylaminopyridine were dissolved In 10mL of tetrahydrofuran, the resulting mixed solution is recorded as solution B, and then solution A and solution B are pumped into the microchannel reaction device according to the flow volume ratio of 1:1, the flow rate is 0.2mL / min respectively, and after being mixed by a Y-shaped mixer Enter the microchannel reactor (the inner diameter of the polytetrafluoroethylene tube of the microreactor is 0.5mm, the volume of the polytetrafluoroethylene tube is 4mL) and react at 130°C for 10min. The organic phase was obtained from the discharge of the microreactor, and the crude product was obtained by vacuum concentration, which was separated by developer column chromatography with a ratio of petroleum ether to ethyl acetate of 20:1 to obt...

Embodiment 3

[0045] 1.5mmol (0.4170g) of (2E,4E)-4-(acetoxyimino)-4-(4-fluorophenyl)but-2-enoic acid ethyl ester, 0.1mmol (0.0099g) of chlorine Cuprous chloride was dissolved in 10 mL of tetrahydrofuran, and the resulting mixed solution was recorded as solution A; 1 mmol (0.0930 g) of aniline, 2 mmol (0.0600 g) of paraformaldehyde and 0.4 mmol (0.0488 g) of 4-methylaminopyridine were dissolved in 10 mL In tetrahydrofuran, the resulting mixed solution is recorded as solution B, and then solution A and solution B are pumped into the microchannel reaction device according to the flow volume ratio of 1:1, and the flow rate is 0.2mL / min respectively. In the channel reactor (the inner diameter of the polytetrafluoroethylene tube of the microreactor is 0.5 mm, and the volume of the polytetrafluoroethylene tube is 4 mL), react at 130° C. for 10 min. The organic phase was obtained from the discharge of the microreactor, and the crude product was obtained by vacuum concentration, which was separated...

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Abstract

The invention discloses a method for synthesizing a dihydroimidazole compound, which comprises the following steps: by taking an alpha, beta-unsaturated ketoxime ester compound I, an aniline compound II and paraformaldehyde III as reaction raw materials, adding a catalyst and an alkaline additive, and preparing a dihydroimidazole compound IV by utilizing a micro-channel modular reaction device, compared with the prior art, the novel dihydroimidazole compound is prepared by taking the alpha, beta-unsaturated ketoxime ester compound, paraformaldehyde and aniline compound as substrates, and the product is rapidly and efficiently synthesized by using a cheap metal catalyst. Wherein R1 and R2 are independently selected from non-substituted or substituted phenyl or thienyl, and the substituted phenyl is selected from phenyl substituted by halogen, nitryl, C1-C5 alkyl or C1-C5 alkoxy.

Description

technical field [0001] The invention belongs to the technical field of synthesis of dihydroimidazole compounds, and in particular relates to a method for synthesizing dihydroimidazole compounds by using a microchannel reaction device. Background technique [0002] Substituted dihydroimidazole compounds are an important class of heterocyclic compounds for the construction of natural products, functional materials, and ligands for organometallic catalysts. Therefore, people are devoting themselves to developing new transformation methods to construct various dihydroimidazole derivatives. [0003] At present, the preparation methods of dihydroimidazole derivatives mainly include: (1) boron trifluoride diethyl ether triggers the rapid condensation of multifunctional isocyanide structural units and π electrophiles to obtain substituted dihydroimidazoles, which can be found in the literature (J. Org.Chem.2020,85,14,9153–9160); (2) It was reported that iodine-mediated benzimidazol...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D233/26C07D409/04B01J19/00B01F33/30
CPCC07D233/26C07D409/04B01J19/0093
Inventor 乔凯段金电徐高晨黄达李玉光郭凯
Owner NANJING ADVANCED BIOLOGICAL MATERIALS & PROCESS EQUIP INST CO LTD
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